Search results for "Esters"
showing 10 items of 305 documents
Development of polymer-based nanoparticles for Zileuton delivery to the lung : PMeOx and PMeOzi surface chemistry reduces interactions with mucins
2021
In this paper, two amphiphilic graft copolymers were synthesized by grafting polylactic acid (PLA) as hydrophobic chain and poly(2-methyl-2-oxazoline) (PMeOx) or poly(2-methyl-2-oxazine) (PMeOzi) as hydrophilic chain, respectively, to a backbone of α,β-poly(N-2-hydroxyethyl)-D,L-aspartamide (PHEA). These original graft copolymers were used to prepare nanoparticles delivering Zileuton in inhalation therapy. Among various tested methods, direct nanoprecipitation proved to be the best technique to prepare nanoparticles with the smallest dimensions, the narrowest dimensional distribution and a spherical shape. To overcome the size limitations for administration by inhalation, the nano-into-micr…
Antimicrobial additives for poly(lactic acid) materials and their applications: current state and perspectives
2018
Poly(lactic acid)-based antimicrobial materials received considerable attention as promising systems to control microbial growth. The remarkable physicochemical properties of PLA such as renewability, biodegradability, and US Food and Drug Administration (FDA) approval for clinical use open up interesting perspectives for application in food packaging and biomedical materials. Nowadays, there is an increasing consumer demands for fresh, high-quality, and natural foods packaged with environmentally friendly materials that prolong the shelf life. The incorporation of antimicrobial agents into PLA-based polymers is likely to lead to the next generation of packaging materials. The development o…
Microbial production of biopolymers from the renewable resource wheat straw.
2014
Aims Production of poly-s-hydroxybutyrate (PHB) and the chemical basic compound lactate from the agricultural crop ‘wheat straw’ as a renewable carbon resource. Methods and Results A thermal pressure hydrolysis procedure for the breakdown of wheat straw was applied. By this means, the wheat straw was converted into a partially solubilized hemicellulosic fraction, consisting of sugar monomers, and an insoluble cellulosic fraction, containing cellulose, lignin and a small portion of hemicellulose. The insoluble cellulosic fraction was further hydrolysed by commercial enzymes in monomers. The production of PHB from the sugar monomers originating from hemicellulose or cellulose was achieved by …
Effects of indole-3-acetic acid on Sinorhizobium meliloti survival and on symbiotic nitrogen fixation and stem dry weight production
2009
We evaluated the effects of the main auxin phytohormone, indole-3-acetic acid (IAA), on the central metabolism of Sinorhizobium meliloti strain 1021. We either treated the Sinorhizobium meliloti 1021 strain with 0.5 mM IAA (1021+) or use a derivative, RD64, of the same strain harbouring a pathway for IAA biosynthesis converting tryptophan into IAA via indoleacetamide. We assayed the activity of key enzymes in the major energy-yielding pathways (Entner-Doudoroff, Embden-Meyerhof-Parnas, pentose phosphate, glyoxylate bypass and tricarboxylic acid cycle). We found that activity of two main regulative tricarboxylic acid (TCA) cycle enzymes was increased. Citrate synthase (CS) activity, as compa…
PEGYLATED POLYASPARTAMIDE–POLYLACTIDE BASED NANOPARTICLES PENETRATING CYSTIC FIBROSIS ARTIFICIAL MUCUS
2016
Here, the preparation of mucus-penetrating nanoparticles for pulmonary administration of ibuprofen in patients with cystic fibrosis is described. A fluorescent derivative of α,β-poly(N-2-hydroxyethyl)-D,L-aspartamide is synthesized by derivatization with rhodamine, polylactide, and poly(ethylene glycol), to obtain polyaspartamide− polylactide derivatives with different degrees of pegylation. Starting from these copolymers, fluorescent nanoparticles with different poly(ethylene glycol) content, empty and loaded with ibuprofen, showed spherical shape, colloidal size, slightly negative ζ potential, and biocompatibility toward human bronchial epithelial cells. The high surface poly(ethylene gly…
Functionalization of Active Ester-Based Polymersomes for Enhanced Cell Uptake and Stimuli-Responsive Cargo Release
2016
Poly(2,3-dihydroxypropyl methacrylamide) (P(DHPMA))-based amphiphilic block copolymers have recently proven to form polymer vesicles (polymersomes). In this work, we further expand their potential by incorporating (i) units for pH-dependent disintegration into the hydrophobic membrane and (ii) mannose as targeting unit into the hydrophilic block. This last step relies on the use of an active ester prepolymer. We confirm the stability of the polymersomes against detergents like Triton X-100 and their low cytotoxicity. The incorporation of 2-(2,2-dimethyl-1,3-dioxolane-4-yl)ethyl methacrylate into the hydrophobic block (lauryl methacrylate) allows a pH-responsive disintegration for cargo rele…
Sequential conversion of orthogonally functionalized diblock copolymers based on pentafluorophenyl esters
2010
Statistic and block copolymers exhibiting activated ester side groups were synthesized by reversible addition-fragmentation chain transfer polymerization in the presence of cumyl dithiobenzoate, benzyl dithiobenzoate, and 4-cyano-4-((thiobenzoyl)sulfanyl)pentanoic acid as chain transfer agents. Pentafluorophenyl methacrylate and pentafluorophenyl 4-vinylbenzoate were used to enable a sequential functionalization of the obtained copolymers by conversion of the activated esters with different amines. 1H NMR spectroscopy, 19F NMR spectroscopy, and FTIR spectroscopy showed the successful step-by-step conversion of the different activated esters by aniline followed by aliphatic amines, thereby r…
When Functionalization of PLA Surfaces Meets Thiol−Yne Photochemistry: Case Study with Antibacterial PolyaspartamideDerivatives
2014
International audience; In this work we wish to report on the covalent functionalization of polylactide (PLA) surfaces by photoradical thiol–yne to yield antibacterial surfaces. At first, hydrophilic and hydrophobic thiol fluorescent probes are synthesized and used to study and optimize the conditions of ligation on alkyne-PLA surfaces. In a second part, a new antibacterial polyaspartamide copolymer is covalently grafted. The covalent surface modification and the density of surface functionalization are evaluated by SEC and XPS analyses. No degradation of PLA chains is observed, whereas covalent grafting is confirmed by the presence of S2p and N1s signals. Antiadherence and antibiofilm acti…
Joining Two Natural Motifs: Catechol-Containing Poly(phosphoester)s.
2017
Numerous catechol-containing polymers, including biodegradable polymers, are currently heavily discussed for modern biomaterials. However, there is no report combining poly(phosphoester)s (PPEs) with catechols. Adhesive PPEs have been prepared via acyclic diene metathesis polymerization. A novel acetal-protected catechol phosphate monomer was homo- and copolymerized with phosphoester comonomers with molecular weights up to 42000 g/mol. Quantitative release of the catechols was achieved by careful hydrolysis of the acetal groups without backbone degradation. Degradation of the PPEs under basic conditions revealed complete and statistical degradation of the phosphotri- to phosphodiesters. In …
HPMA copolymers as surfactants in the preparation of biocompatible nanoparticles for biomedical application.
2012
In this work we describe the application of amphiphilic N-(2-hydroxypropyl)methacrylamide (HPMA)-based copolymers as polymeric surfactants in miniemulsion techniques. HPMA-based copolymers with different ratios of HPMA (hydrophilic) to laurylmethacrylate (LMA; hydrophobic) units were synthesized by RAFT polymerization and postpolymerization modification. The amphiphilic polymers can act as detergents in both the miniemulsion polymerization of styrene and the miniemulsion process in combination with solvent evaporation, which was applied to polystyrene and polylactide. Under optimized conditions, monodisperse colloids can be prepared. The most promising results could be obtained by using the…